This invention relates to the antibiotic 3-halo-1azabicyclo[3.2.0]hept-2-ene-7-one-2-carboxylic acid (I) and to its pharmaceutically acceptable salt, ester and amide derivatives: ##STR2## wherein X is halo, such as chloro or bromo.
The compounds of the present invention (I) are also useful as intermediates in the preparation of the 6-(1'-hydroethyl)-3-substituted-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carbo xylic acids which are also antibiotics; such compounds are disclosed in commonly assigned U.S. patent application Ser. No. 000,470 filed Jan. 2, 1979 which is a continuation of U.S. patent apolication Ser. No. 843,620 filed Oct. 19, 1977, now abandoned, which application is incorporated herein by reference.
This invention also relates to processes for the preparation of such compounds (I); pharmaceutical compositions comprising such compounds; and to methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
There is a continuing need for new antibiotics. For unfortunately, there is no static effectiveness of any given antibiotic because continued wide scale usage selectively gives rise to resistant strains of pathogens. In addition, the known antibiotics suffer from the disadvantage of being effective only against certain types of microorganisms. Accordingly the search for new antibiotics continues.
Thus, it is an object of the present invention to provide a novel class of antibiotics and intermediates to antibiotics which are useful in animal and human therapy and in inanimate systems. These antibiotics are active against a broad range of pathogens which representatively include both gram positive bacteria such as S. aureus, Strep. pyogenes and B. subtilis, and gram negative bacteria such as E. coli, Proteus morganii, Pseudomonas, Serratia and Klebsiella. Further objects of this invention are to provide chemical processes for the preparation of such antibiotics and their non-toxic pharmaceutically acceptable salts; pharmaceutical compositions comprising such antibiotics; and to provide methods of treatment comprising administering such antibiotics and compositions when an antibiotic effect is indicated.